Borrelidin, threonyl-tRNA synthetase inhibitor

Key facts

CAS number

7184-60-3

Purity

>98%

Form

Solid

form

Source

Streptomyces sp.

Molecular weight

489.6 Da

Molecular formula

C₂₈H₄₃NO₆

PubChem

6436801

Nature

Native

Biochemical name

Borrelidin

Biological description

Potent antiangiogenic agent (IC₅₀ = 0.8 nM, rat aorta). Selective threonyl-tRNA synthetase inhibitor. Antibiotic agent. CDK inhibitor. Induces apoptosis in capillary tube-forming endothelial cells. Disrupts capillary tubes and inhibits their formation. Shows antiviral and antifungal effects. Shows antiangiogenic effects in vivo.

Canonical smiles

CC1CC(CC(C(C(=CC=CCC(OC(=O)CC(C(C1)C)O)C2CCCC2C(=O)O)C#N)O)C)C

Isomeric smiles

C[C@H]1C[C@H](C[C@@H]([C@H](/C(=C\C=C\C[C@H](OC(=O)C[C@@H]([C@H](C1)C)O)[C@@H]2CCC[C@H]2C(=O)O)/C#N)O)C)C

InChi

InChI=1S/C28H43NO6/c1-17-12-18(2)14-20(4)27(32)21(16-29)8-5-6-11-25(22-9-7-10-23(22)28(33)34)35-26(31)15-24(30)19(3)13-17/h5-6,8,17-20,22-25,27,30,32H,7,9-15H2,1-4H3,(H,33,34)/b6-5+,21-8-/t17-,18+,19-,20-,22+,23+,24-,25-,27+/m0/s1

InChiKey

OJCKRNPLOZHAOU-UGKRXNSESA-N

IUPAC Name

(1R,2R)-2-[(2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid